Destiel Fun Run
by Speary
Summary: Dean is an executive that decides to get his co-workers to volunteer for a Fun Run for little girls. Each of them will be a running buddy, and Dean is woefully unprepared for this type of physical activity. This is a Dean Smith AU/Destiel/One-shot. And if you want to you can call it a crossover with The Office.


Dean Smith was a genius in so many ways. Cas thought this not for the first time as he watched Dean handing out racing bibs in the parking lot that morning. This moment though, was not an example of Dean's genius though. Put the guy in the board room with a room full of bored suits and Dean will charm them all into submission. He'll convince them that the company can meet all their needs and that they should just sign on the dotted line. It all came to him so easily.

If you hand Dean a stack of nearly incomprehensible reports, he'll have them figured out within hours, along with a detailed explanation for one Cas Novak so that he won't feel like an idiot in the future. They worked well together. He had an office down the hall, and Dean was his boss, sort of. He never treated Cas like an underling, so sometimes the lines were a little blurry on whether or not they were friends or just co-workers, or, and Cas shuddered with the thought, boss and employee. There had been a Christmas party not so long ago that had tested the boundaries of their maybe friendship, but Cas chose not to think about that too much. Dean had been drunk and had not brought it up since, so who was he to mention it.

He caught a glance from Dean and a smile spread across his own lips as the man began walking toward him, racing bib in hand. "Hey Cas."

"Hello, Dean." Cas was always struck by how much Dean's smile brightened something within him. It was a glow of absolute sunshine paired with the most mesmerizing green eyes a person could have. It was almost unfair.

Dean reached out to his shirt and started pinning the racing bib to the front, just above the hemline. Number 210. "Number buddies," Dean said with a smile, pointing down at his own number, 211. "So, where is your running buddy?"

"She's over there with her friends, getting her hair painted or something. I'm going to join her in a bit. Where's yours?"

"She's over there." Dean waved a casual hand behind him and looked a little less gleeful in the moment. "Pretty sure she doesn't like me. She asked me if I had prepared for the even, and I told her yes. Then she wanted to know what I had done, and I guess she didn't like my answer. She's been avoiding me ever since."

Cas laughed a little and had to ask, "So, what have you been doing to prepare?"

"Oh, tons." Dean sounded jolly again and maybe a little full of himself. "I've been hitting the racquetball court with Sam, and I totally did some lifting this week. Plus, I have my martial arts."

"No running?" Cas was all smiles now. The thought of Dean preparing for a run by not running spoke to his not being a genius in this field.

"Nah, I wanted to be fresh. I loaded up on carbs this morning." Dean ran a hand up through his hair and added, "Pasta, the breakfast of champions." Cas had to laugh at that.

"This is going to be rough on you. No wonder your running buddy is concerned." Cas was looking about for his running buddy, a 9 year old girl paired with him by the organization. Dean had decided that the execs would participate in a charity run for a local girl's running group. The group worked to increase female empowerment and self-worth in young girls. Each girl that went through the program ended by participating in a 5k. The catch was that each girl needed a running buddy for the race. Dean had heard about a local foster shelter that had participated in the program. None of the girls from the shelter had running buddies. In no time flat, Dean found his cause. It took almost nothing to convince the others to participate.

Cas was quick to volunteer and Sam jumped in too. Sam was already at the hair station with his running buddy. They were spraying generous quantities of pink and green over his long hair. Cas walked over, Dean in his wake. "Looking good, Sam."

"Yeah, I wanted to match my buddy here. Dean, Cas, meet Ruby. She's going to be a demon on the trail. You all better watch yourselves." Sam reached over and gave her a pat and she smiled at him, clearly pleased with the praise.

"Nice to meet you Ruby." Cas said as he took a seat next to her. He looked to the seat next to his and noticed that his running buddy was just finished and was now getting a fake tattoo. She looked at him and smiled.

"You getting a bit of color too?"

"Looks like it. Should we match?" Cas smiled at her and she returned it.

"Yeah, that would be cool."

Cas told the volunteer to match Anna's color. She had a long pile of red hair, now with purple and green streaks. "Dean, Ruby, Sam, this is Anna." He lifted his hand to the others as the volunteer began spraying color into his hair. Dean's running buddy joined them then, her hair a vibrant shade of orange on blonde locks.

"So, grandpa, you gonna get a little color?" Dean's running buddy smirked.

Dean seemed to push down the frown that came to him at being called grandpa. Instead he turned up the charm and plopped himself in the chair next to Cas saying, "Sure thing kiddo. Give me the orange treatment." He smiled at her and she frowned at the use of the word kiddo. "Everybody, this is Claire. Claire this is Cas, Ruby, Anna, and Sam." Dean pointed at each in turn.

The announcer called out the time. They had 5 minutes left before the run. Claire gave Cas a once over. "You run?"

"Often." He answered simply.

"Why didn't we get paired up?" She looked back at Dean.

"Hey, I'm totally ready for this. You just watch. I'm going to leave them in the dust." Dean smiled over at Cas, and Cas had to admire his confidence.

"He ate a bunch of fettuccine alfredo for breakfast as preparation. I'm pretty sure he's going to die by the first mile." Claire looked to Cas for support.

"You are probably right, but let's not make him feel bad about it just yet." Cas gave her a warm smile and turned to Dean with a little sympathy in his eyes.

"Ah, man. Way to throw a guy under the bus." Dean's hair was completely orange now. He got up and Sam and Cas followed.

"It might not be so bad." Sam clapped a hand on Dean's back. "At least you can take pride in getting us all out here today. If it weren't for you, most of us would be sitting in a dusty office filling out expense reports. This is way better."

"Too true," Cas added.

Claire looked at Dean out of the corner of her eyes then. "So, you're the guy that organized the volunteers for the shelter girls?"

"Yeah." Dean was still bristling from the comments before, but he was doing his best to cover.

"You're doing great today," Claire offered.

"We haven't started yet," Dean cocked his head to the side as he replied.

"I know." Claire began stretching and Dean copied her with a thin smile on his face.

He turned to Cas and said in a low whisper. "She might be right. I'm not sure I'll be doing much good out there. Maybe you should just take my girl on too."

"Nope, you're doing this. We have your back." Cas squeezed Dean's shoulder and hoped to impart some pre-running enthusiasm in the gesture.

A few minutes later and the announcer began the countdown. The run began, not as a run, but more as a slow ooze through the starting gate. "Oh, this is easy. I got this." Dean smiled over to Cas, clearly not considering the way that things would pick up once the crowd spread out more.

The crowd spread out a little and Cas noticed that his running buddy was fast. He picked up the pace a bit and matched her steps. He looked to his left and saw that Claire and Dean were there at his side. The collective sound of feet on pavement gave him a rhythm to match. He could feel his heart rate kicking up. "You're doing good, Anna." She smiled up at him.

Ruby darted past them in a sea of wild hair and flailing arms. Sam was keeping up with her easily. "Come on Sam." Ruby encouraged him needlessly.

The two of them raced away past the crowd. Cas looked down at Anna, who huffed out, "We can go faster if you want."

"I'm in no hurry. You set the pace, and I'll keep up." Cas wasn't even winded. This was easy for him. Anna did not speed up.

After the first mile, Cas heard Claire's voice from behind him, "Come on Dean. You can do this." It was a little backwards. The buddies were supposed to encourage the girls. Cas chanced a look back and noticed that Dean was looking a little pale. He was certainly slowing up.

"Stick with Cas." Dean was breathing hard as he said this. "I'll catch up." He was slowing to almost a walk. Claire looked back to Cas and jogged up alongside of him.

"So, what should I do?" They kept jogging along, Dean dropping back farther and farther with each step.

"I think that you should keep going. He'll be fine." Cas threw one more look back and saw Dean heading off to the edge of the trail to off load the breakfast of champions. Cas turned back to the path ahead. "Yeah, we should definitely keep on going."

They crossed the finish line with 32 minute records. _Not too bad._ Cas had thought as he walked Anna over to the awards. Claire was with them and picked her's up too. "You think that he is almost done?"

"Not sure." Cas looked out over the crowds and saw Sam and Ruby sucking down red cones of shaved ice. They walked over to them. "What was your time?" Cas asked good naturedly.

"We rocked," Ruby practically bounced alongside Sam. "We got here in 29 minutes."

"Wow, that is impressive." Cas smiled at her.

"Where's Dean?" Sam looked past them both to see if Dean was lingering in the background somewhere.

Claire chose to answer for them. "He's still running or walking. He wasn't feeling so hot."

Sam's lip curled up in a little smirk. Cas felt like maybe he should go find Dean. "Sam, I think I'm going to go find Dean. Help him along a little. You mind watching Anna and Claire?"

"I'm going with you. He's my buddy after all." Claire had a look of determination on her face.

"Okay, just Anna then." He looked down at Anna. "Make sure that Sam gets you one of the shaved ice things." She smiled at him then at Sam.

"Come on kid' let's get you some sugary ice." Sam took her hand and he and Ruby bounded off into the crowd.

"So, should we run the course backwards?" Claire looked back at the finish line.

"No, we don't want to disrupt the race. We just need to be a little quick. You got enough energy for this?" He cocked his head to the side as he asked.

"Totally. I could have done this in my sleep." She started running off in the direction of the starting point of the trail. Cas ran off behind her, catching up with ease. Fifteen minutes into the run and they came to Dean, just sitting on the side of the trail, not far from where they had left him. He looked pale and sad. They both slowed up and stood in front of him.

"Hey, Dean." Cas crouched down in front of him. Dean raised his head up from gazing at his shoes.

"Guess I shouldn't have eaten all of that pasta." Dean looked back down at his shoes.

Cas said, "Well, normally, you are a genius. Today, not so much. Mistakes were made." He stood then and held a hand out to Dean. "Now, you just have to make it back to the start. Let's get to the finish line."

Dean looked up at him then at Claire. "I don't have anything left in me. You guys go on, get to the end."

Claire spoke up then. "We already did, Dean. It isn't that far. We just came back to get you. So, come on." She held out a hand now too.

"I'll make it back eventually." Dean sounded all kinds of pathetic now. Cas thought that it might be hard to convince him to just get up.

Claire said, "You gotta get up, Dean. Cas was all kinds of worried about you, and I am sure that he'll just sit there at the finish line until you show up. So, you should probably get up and try, for his sake."

"I was not…"

Claire cut him off though, "Shh, you so were." She gave him a wink and looked back at Dean then. "So come on grandpa. Get up." She reached out to his hand and gave him a mighty pull for one so young. Dean swooped up. and the three of them began wandering along the trail.

"See, now that isn't so bad." Cas smiled over at Dean's still pale face.

"Yeah, except for the humiliation." He looked away from Cas and plodded along.

"No one will know, except for the two of us. I think that Claire and I can keep it under wraps."

"Kinda don't care about everyone else's opinions so much." Dean was muttering now.

"Well, I don't think any less of you, if that helps." Cas raised a hand to Dean's shoulder and gave it a squeeze of affection. "You did a lot of good today."

Claire reached up and squeezed Dean's other shoulder. "Yeah, you sure did." Dean smiled a little with the words and his steps brought him closer to Cas. Their shoulders brushed with each step. Dean was looking less pale. Cas felt a warm blanket of sorts cover over him as they walked side by side. It would be easy to move his hand down to Dean's, but he wasn't sure how such a gesture would be met. True there had been Christmas, but that was months ago. The shoulder was a safe zone. It was a zone that said, _we're cool buddy, pal, friend._ He didn't want to chance any discomfort.

Claire was looking at them out of the corner of her eyes. Her lips curled up in a hint of a smile. "What?" Cas asked.

"You two are cute is all," she said.

"What do you mean by that?" Dean asked.

"My last foster house was with two guys that wanted to adopt a baby. They took me in for a spell just to be helpful. They looked at each other the way you two look at each other."

Dean stammered a little and Cas said, "Dean and I are just friends...co-workers." He struggled to find the right words.

"So, when you ask him out to dinner tonight is that going to be a friendly date or something more?" She smirked and quickened her pace a little.

Dean looked at Cas confused. "You're planning to ask me out to dinner?"

"I don't know what she is talking about." He watched Dean's expression fall a little. He considered the impact that his words had on Dean and added, "Well, I do need to eat later." Dean looked confused then a little happier. They hit the second mile on the journey back, just one more to go.

"I don't need a charity meal." He turned back to the road ahead and plodded on, increasing his pace a little.

Cas matched him. Claire gave them a little space, smiling as she started jogging ahead. "It wouldn't be charity. I genuinely do need to eat. I did this 5k twice, I'll have you know." Cas was keeping his tone light. He felt the stirring of nerves in his gut though. _Am I really asking him out?_ He thought that he could still pretend that it was a friendly invite if Dean seemed to be bothered by it.

Dean walked on beside him silently. Claire was far off in the distance now, pounding a path toward the finish line for the second time. "She's fast." Dean glanced over at Cas.

"Yep." Cas felt like maybe Dean was just going to pretend that the last couple of minutes never happened. Cas was trying to decide whether or not he was fine with that. He wasn't. He walked on with a look of determination on his face. _Just get back and part ways._

"You okay?" Dean nudged him a little as they walked.

"I'm fine." Cas knew that he sounded irritated, but he couldn't push it down.

"That's what a person says when they aren't. What's up?"

Cas stopped walking. Dean stopped two steps ahead and turned back. "What do you think is wrong with me? Nobody likes being rejected, especially not repeatedly and publicly." Cas started walking again. He passed Dean who seemed to be frozen to the spot. A few seconds passed and Cas could hear the pounding of Dean's shoes on asphalt. He was jogging alongside him.

"Cas, stop." He grabbed Cas' arm. "Stop."

Cas stopped. "Let's just keep going so I can beat a hasty retreat." He paused a beat and added, "Please."

"But then I won't know where we are going to dinner." Dean looked a little worried, like he might get rejected now.

"I don't need a charity meal." Cas threw Dean's words back out at him and continued toward the finish line, shrugging off Dean's hand as he went.

Dean kept up with Cas and said, "It wouldn't be charity. Well, not on my end. I still think that it would be charity on your end though." Cas looked at him then, but kept walking.

"How so?" Cas could see Dean's smile growing a little as he spoke.

"Well, I never do seem to get a chance to reciprocate where you are concerned." They kept walking and Cas could hear his heart beat in his ears. Dean continued, "At Christmas, I thought that you wanted to avoid me because I acted like a drunk fool. I mean, I kissed you and said you were pretty. I sounded like an idiot. No wonder you avoided me when we all got back from the holiday."

"I didn't avoid you. You avoided me. I was in my office the whole time with that stack of reports you handed off to me. You obviously knew where to find me. Plus, you kept calling me buddy all of the time. What was I supposed to think?" Cas didn't realize how irritated he had been about the whole thing. Here it was April and he was sounding like a recently dumped teenager.

"I'm sorry. I thought you had regrets." Dean walked on beside him, maintaining a close proximity despite Cas' slightly angry tone. "I was trying to make it easier. I didn't want to screw up our friendship."

"Well, good job with that." Cas kicked up the pace a little. _Wait, what am I doing?_ He got a few steps ahead and then stopped. Dean nearly ran into him. Cas turned and said, "So, you didn't have regrets?"

"Well, I do now. I should have talked with you. I should have come by your office at least. Maybe played out some of the not safe for work fantasies that I had been harboring." Dean stepped closer. "I'm sorry."

Cas felt a little choked up. "Not safe for work fantasies, huh?"

Dean ran a hand up Cas' arm. "A few."

Cas felt a rush of sorts curl up around him as he stood there staring into Dean's eyes. "Dinner first. Let's get through this 5k."

Dean nodded and said, "Okay." They walked on side by side. The finish line was not much farther ahead. They crossed it and Claire, Sam, Ruby, and Anna were there to cheer. Most everybody else was packing up and leaving.

"You feeling okay, grandpa?" Claire playfully slugged him as he came to a stop in front of them.

"Yeah kiddo. I'm good." He smiled over at Cas. "Even got dinner plans tonight."

She laughed at him and said, "Good on ya. No pasta for you though."

Dean's laughter joined hers. Cas looped an arm around his waist as they left saying, "Maybe a burger though."

Dean said, "Now, that sounds like a smart plan." Claire smiled at them, clearly pleased with the outcome as the group of them made their way out the park.

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**Review, Fav., Rec.**

**AN: Hope you all liked this little piece of fluff. I just finished a run with my daughter and felt inspired. Pretty sure I identify most with Dean at this point.**


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